The Generalissimo

Dear Lisa, as I write this, I am very sad. Our president has been overthrown and [voice changes to that of a man] replaced by the benevolent General Krull. All hail Krull and his glorious new regime! Sincerely, Little Girl.

—The Simpsons, Cape Feare

A Sub-Trope of Evil Overlord, as well as The Caligula. The militaristic leader of a fictional third world state or nation (usually African, South American, Eastern European or Middle Eastern). Almost invariably rules a People's Republic of Tyranny.

His reign tends to be characterised by human rights abuse, political repression, ethnic persecution, extrajudicial killings, nepotism, and corruption. His political viewpoints (if he even has any) veer towards Communism, Fascism, or some combination of the worst aspects of both. Of course, none of this will stop him from proclaiming himself "The People's Liberator" or otherwise billing himself as a great hero. He may have attended a prestigious Ivy League or Oxbridge university in his youth, where he Majored in Western Hypocrisy. He is often the target of American assassination attempts and rebel groups, who may or may not be figments of his own paranoia. A common feature is to have a guerrilla movement training to overthrow them. Once this happens, the general goes into hiding to train his own revolutionaries to overthrow the government, which will be just as corrupt as the old one (as seen in Tintin and the Picaros).

Tends to be based on one or more real-life dictators, most commonly Benito Mussolini, Francisco Franco Joseph Stalin, Fidel Castro, Mao Zedong, Idi Amin, Muammar Gaddafi and Saddam Hussein. This is often used to make an Anvilicious point about said real-life dictator's policies. Surprisingly, Adolf Hitler is rarely parodied in this manner, perhaps because the man himself is enough of an acceptable target (although one of his henchmen, Hermann Goering, did famously dress this way).

Usually dressed in military garb, with a Chest of Medals and topped with a Commissar Cap. Common traits include facial hair of some sort, cigar smoking, a hatred of democracy, a long list of self-bestowed titles, and naming cities and monuments after himself.

Examples of The Generalissimo include:

Comic Books

Tintin has encountered several of these, notably General Alcazar (although he becomes relatively more heroic later) and General Tapioca.
Benoit Brisefer, a French comic, has one such island Banana Republic with three generals (army, navy and air), who are constantly taking and retaking the palace from each other and declaring themselves Arch-Generalissimo or other inflated titles. Meanwhile, the dirt-poor inhabitants have grown used to all this nonsense and carry on life as usual (it helps that the soldiers are all remarkably inept, employing A-Team Firing to the fullest).
In Tex Willer one of their antagonists in a mini arc set in Mexico is basically aiming at this position, but his plans are thwarted and eventually comes back for revenge in another arc.

Film

The Expendables' mission is to eliminate one such general. He is slightly more sympathetic than the usual examples
In The Great Dictator the head of Bacteria was portrayed like this.
In The Three Stooges' shorts making fun of Hitler et al. ("You Nazty Spy" and a sequel or two), Field Marshal Curly was like this.
In the James Bond film, Licence to Kill, Hector Lopez. He is portrayed as more Punch Clock Villain than dictator, as his country is effectively a puppet of The Syndicate.
Emperor Shaddam IV (Jose Ferrer) in the 1984 adaptation of Dune.
Big Bad's main goal in Die Hard 2 was to free a dethroned one for money.
Sacha Baron Cohen's character Admiral General Colonel Doctor Shabazz Aladeen, Democratic President-For-Life, Invincible and All-Triumphant Commander, Chief Ophthalmologist, Brilliant Genius of Humanity, Excellent Swimmer Including Butterfly, and Beloved Oppressor and Ruthless Protector of the Precious and Expendable People of Wadiya from The Dictator is a outrageously over the top example that makes every other example on this page look downright subtle and nuanced, as made clear in his biography.

Literature

Mentioned by Terry Pratchett in Lords and Ladies as "Some people are born to kingship. Some achieve kingship, or at least Arch-Generalissimo-Father-of-His-Countryship.", possibly referring to Franco.
"Mad Dog" Branzillo of A Swiftly Tilting Planet rules the fictional South American country Vespugia. The plot revolves around going back in time and changing events so that Branzillo becomes a benevolent ruler instead.
The Autumn of the Patriarch as the dictator (unnamed) as its protagonist.
The Feast of the Goat gives us the real-life Rafael Trujillo.

Live-Action TV

Parodied in an episode of 30 Rock. Elisa's (Salma Hayek) grandmother hates Jack because he bears a striking resemblance to the Generalissimo, the villain of her favorite soap opera. Jack (being the President of NBC) acquires Telemundo and attempts to have the Generalissimo killed off. Unfortunately, since the show is apparently broadcast live, the actor playing the Generalissimo goes Off the Rails when the female protagonist attempts to shoot him.

[subtitled in Spanish] "Ha! You missed! Now I shall drink this magic potion that will allow me to live forever!"

Music

"Weird Al" Yankovic is tasked with assassinating no less than two of these types in his "Party in the C.I.A" video. But one of them ends up killing him.

Video Games

You play as one of these in Tropico.
Street Fighter: M. Bison
Battlefield: Bad Company 1 has Zavomir Serdar, dictator of the fictional country Serdaristan. His role is mostly comic relief and The Load to B Company.
General Viper in Chrono Cross, who rules El Nido with his Acacia Dragoons. He's actually a rare heroic example; he might be authoritarian, but he's a good ruler and was only after Serge because he was being manipulated by Lynx.
Alvaro Sosa from 7.62: High Calibre has taken over the small Latin American country the game takes place in by coup. A rare example of one shown with Gray and Gray Morality as a good portion of the population considers all of the country's previous post-Spanish rulers terrible and believes he is the best hope for a functional government. He fights against the equally nasty communist guerrillas.

Western Animation

The Simpsons: All hail Krull and his glorious new regime!
Roger briefly impersonates one of these in American Dad.
Transformers Generation 1 had Abdul Fakkadi, Supreme Military Commander, President-for-Life, and King of Kings of the Socialist Democratic Federated Republic of Carbombya, a not-so-subtle Take That at Muammar Gaddafi (with his long list of titles a probable reference to Idi Amin).

Other Media

After the fiasco of the 2000 Presidential election, The Onion ran a shot of Bill Clinton photoshopped into a Generalissimo uniform with the title "Clinton declares Self Presidente for Life."